Menu

Top 10 Best Hawaii Sailing Trips

Found 109 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 2
 

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

(4.9 of 961 reviews)

2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island of Oahu since 1985... More

Free Cancellation
Start From $59.98
 
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

  • Hawaii
  • Superb961 reviews4.9

2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....

    Free Cancellation
    Start From $59.98
 
 

Kauai’s Na Pali Coast Snorkel and Sail Tour

(4.8 of 568 reviews)

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making it the top choice for fami... More

Free Cancellation
Start From $292.48
 
Kauai’s Na Pali Coast Snorkel and Sail Tour Likely to Sell Out

Kauai’s Na Pali Coast Snorkel and Sail Tour

  • Hawaii
  • Superb568 reviews4.8

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour cat....

    Free Cancellation
    Start From $292.48
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 841 reviews)

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More

Free Cancellation
Start From $213.41
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • Hawaii
  • Superb841 reviews4.7

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....

    Free Cancellation
    Start From $213.41
 
 

Paragon Lahaina Sunset Sail

(4.8 of 18 reviews)

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the glassy, miraculous ‘au’au Channel is like floating inside an infinite ... More

Free Cancellation
Start From $102.00
 
Paragon Lahaina Sunset Sail Likely to Sell Out

Paragon Lahaina Sunset Sail

  • Hawaii
  • Superb18 reviews4.8

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from L....

    Free Cancellation
    Start From $102.00
 
 

Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

(4.6 of 20 reviews)

Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, socialize with friends and family and take in the spectacular Maui sunset.... More

Free Cancellation
Start From $59.95
 
Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor Likely to Sell Out

Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

  • Hawaii
  • Superb20 reviews4.6

Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, ....

    Free Cancellation
    Start From $59.95
 
 

Waikoloa Signature Catamaran Sunset Sail

(4.7 of 413 reviews)

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers a smooth, comfortable ride with panoramic views of Mauna Kea... More

Free Cancellation
Start From $159.00
 
Waikoloa Signature Catamaran Sunset Sail Likely to Sell Out

Waikoloa Signature Catamaran Sunset Sail

  • Hawaii
  • Superb413 reviews4.7

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. De....

    Free Cancellation
    Start From $159.00
 
 

Day's End Cocktail Sunset Sail

(4.7 of 87 reviews)

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. This isn’t a dinner cruise, it’s happy hour reimagined (a true ‘pau hana’ at sea) with handcrafted drin... More

Free Cancellation
Start From $159.00
 
Day's End Cocktail Sunset Sail Likely to Sell Out

Day's End Cocktail Sunset Sail

  • Hawaii
  • Superb87 reviews4.7

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....

    Free Cancellation
    Start From $159.00
 
 

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

(4.8 of 308 reviews)

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More

Free Cancellation
Start From $72.96
 
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea Likely to Sell Out

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

  • Hawaii
  • Superb308 reviews4.8

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....

    Free Cancellation
    Start From $72.96
 
 

Kona Tradewind Catamaran Day Sail

(4.8 of 47 reviews)

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails as you glide across the water, taking in panoramic views of volcanic cliffs, sparklin... More

Free Cancellation
Start From $89.00
 
Kona Tradewind Catamaran Day Sail Likely to Sell Out

Kona Tradewind Catamaran Day Sail

  • Hawaii
  • Superb47 reviews4.8

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing ca....

    Free Cancellation
    Start From $89.00
 
 

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

(4.7 of 966 reviews)

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More

Free Cancellation
Start From $84.99
 
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure Likely to Sell Out

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....

  • Hawaii
  • Superb966 reviews4.7

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....

    Free Cancellation
    Start From $84.99
 
 

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

(4.9 of 208 reviews)

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

Special Offer
Free Cancellation
Start From $63.20
(Saving 20% ) $79.00
 
-20% Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming Likely to Sell Out

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

  • Hawaii
  • Superb208 reviews4.9

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....

    Special Offer
    Free Cancellation
    Start From $63.20
    (Saving 20% ) $79.00
 
 

Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

(4.9 of 103 reviews)

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers, and ocean lovers, this Lahaina adventure combines a... More

Special Offer
Free Cancellation
Start From $163.20
(Saving inf% ) $0.00
 
-inf% Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar Likely to Sell Out

Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

  • Hawaii
  • Superb103 reviews4.9

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury ....

    Special Offer
    Free Cancellation
    Start From $163.20
    (Saving inf% ) $0.00
 
 

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

(4.8 of 220 reviews)

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More

Special Offer
Free Cancellation
Start From $200.00
(Saving inf% ) $0.00
 
-inf% Molokini Snorkel and Performance Sail: Mā’alaea Harbor Likely to Sell Out

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

  • Hawaii
  • Superb220 reviews4.8

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....

    Special Offer
    Free Cancellation
    Start From $200.00
    (Saving inf% ) $0.00
 
 

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

(4.8 of 58 reviews)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More

Special Offer
Free Cancellation
Start From $289.00
(Saving inf% ) $0.00
 
-inf% Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only) Likely to Sell Out

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

  • Hawaii
  • Superb58 reviews4.8

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....

    Special Offer
    Free Cancellation
    Start From $289.00
    (Saving inf% ) $0.00
 
 

Snorkel with Manta Rays Guaranteed

(4.8 of 751 reviews)

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More

Special Offer
Free Cancellation
Start From $141.57
(Saving inf% ) $0.00
 
-inf% Snorkel with Manta Rays Guaranteed Likely to Sell Out

Snorkel with Manta Rays Guaranteed

  • Hawaii
  • Superb751 reviews4.8

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....

    Special Offer
    Free Cancellation
    Start From $141.57
    (Saving inf% ) $0.00
 
 

Waikiki Fireworks Cocktail Cruise

(4.5 of 8 reviews)

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to remember.... More

Special Offer
Free Cancellation
Start From $85.09
(Saving inf% ) $0.00
 
-inf% Waikiki Fireworks Cocktail Cruise Likely to Sell Out

Waikiki Fireworks Cocktail Cruise

  • Hawaii
  • Exellent8 reviews4.5

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a b....

    Special Offer
    Free Cancellation
    Start From $85.09
    (Saving inf% ) $0.00
 
 

Sunset Cocktail Cruise on our Sailing Catamaran

(4.8 of 64 reviews)

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohala Coast aboard our legendary sailing catamaran Seasmoke. This cruise includes unlimited soft drinks, tropical juices, beers, wines... More

Special Offer
Free Cancellation
Start From $165.00
(Saving inf% ) $0.00
 
-inf% Sunset Cocktail Cruise on our Sailing Catamaran Likely to Sell Out

Sunset Cocktail Cruise on our Sailing Catamaran

  • Hawaii
  • Superb64 reviews4.8

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohal....

    Special Offer
    Free Cancellation
    Start From $165.00
    (Saving inf% ) $0.00
 
 

2-Hour Oahu Sunset Catamaran Sail

(4.8 of 134 reviews)

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for ... More

Special Offer
Free Cancellation
Start From $130.00
(Saving inf% ) $0.00
 
-inf% 2-Hour Oahu Sunset Catamaran Sail Likely to Sell Out

2-Hour Oahu Sunset Catamaran Sail

  • Hawaii
  • Superb134 reviews4.8

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran fr....

    Special Offer
    Free Cancellation
    Start From $130.00
    (Saving inf% ) $0.00
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 864 reviews)

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays!  Upon arriving, receive an in... More

Special Offer
Free Cancellation
Start From $154.51
(Saving inf% ) $0.00
 
-inf% Sunset and Manta Ray Snorkel Adventure Likely to Sell Out

Sunset and Manta Ray Snorkel Adventure

  • Hawaii
  • Superb864 reviews4.9

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....

    Special Offer
    Free Cancellation
    Start From $154.51
    (Saving inf% ) $0.00
 
 

Waikiki Sunset Cruise from Oahu

(4.7 of 66 reviews)

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point to observe marine life such as dolphins, whales, sea... More

Special Offer
Free Cancellation
Start From $45.00
(Saving inf% ) $0.00
 
-inf% Waikiki Sunset Cruise from Oahu Likely to Sell Out

Waikiki Sunset Cruise from Oahu

  • Hawaii
  • Superb66 reviews4.7

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks an....

    Special Offer
    Free Cancellation
    Start From $45.00
    (Saving inf% ) $0.00
 
1 2 3 4 5
Booking.com
Booking.com
Booking.com